Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents

Hisato Shimizu; Akira Yoshimura; Keiichi Noguchi; Victor N Nemykin; Viktor V Zhdankin; Akio Saito

doi:10.3762/bjoc.14.39

Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents

Beilstein J Org Chem. 2018 Feb 28:14:531-536. doi: 10.3762/bjoc.14.39. eCollection 2018.

Authors

Hisato Shimizu¹, Akira Yoshimura^{2

3}, Keiichi Noguchi⁴, Victor N Nemykin⁵, Viktor V Zhdankin², Akio Saito¹

Affiliations

¹ Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan.
² Department of Chemistry and Biochemistry, University of Minnesota, Duluth, MN 55812, USA.
³ The Tomsk Polytechnic University, Tomsk 634050, Russia.
⁴ Instrumentation Analysis Center, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan.
⁵ Department of Chemistry, University of Manitoba, Winnipeg, MB R3T 2N2, Canada.

Abstract

[Bis(trifluoroacetoxy)iodo]benzene (BTI) and (diacetoxyiodo)benzene (DIB) efficiently promote the formation of acylnitroso species from hydroxamic acids in the presence of various dienes to give the corresponding hetero-Diels-Alder (HDA) adducts in moderate to high yields. The present method could be applied to the HDA reactions of acylnitroso species with o-benzoquinones generated by the oxidative dearomatization of guaiacols.

Keywords: acylnitroso; benzoquinone; cycloaddition; dearomatization; iodine(III).